5,6-Dichloro-2-(3-methoxy-phen-yl)isoindoline-1,3-dione.

The title compound, C(15)H(9)Cl(2)NO(3), crystallizes as an inversion twin, the ratio of the twin components being 0.43 (13):0.57 (13). The isoindoline group is planar and inclined by 77.63 (3)° to the aromatic ring substituent. The crystal structure is stabilized by aromatic π-π stacking inter-actions involving the benzene rings of adjacent isoindoline groups, with a centroid-centroid distance of 3.664 (7) Å and an inter-planar separation of 3.409 Å.

Related literature

For general background, see: Chapman et al. (1979 ▶); Hall et al., (1983 ▶; 1987 ▶); Srivastava et al. (2001 ▶); Abdel-Hafez (2004 ▶); Sena et al. (2007 ▶).

Experimental

Crystal data

C15H9Cl2NO3

M = 322.13

Orthorhombic,

a = 6.8689 (5) Å

b = 9.7362 (10) Å

c = 20.4271 (14) Å

V = 1366.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.65 × 0.51 × 0.23 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.685, T max = 0.888

6123 measured reflections

2687 independent reflections

2076 reflections with I > 2σ(I)

R int = 0.117

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.169

S = 1.00

2687 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.57 e Å−3

Absolute structure: Flack (1983 ▶), 1114 Friedel pairs

Flack parameter: 0.43 (13)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010659/rz2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010659/rz2205Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H9Cl2NO3	F000 = 656
Mr = 322.13	Dx = 1.566 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6123 reflections
a = 6.8689 (5) Å	θ = 2.0–27.3º
b = 9.7362 (10) Å	µ = 0.48 mm−1
c = 20.4271 (14) Å	T = 296 K
V = 1366.1 (2) Å3	Prism, colourless
Z = 4	0.65 × 0.51 × 0.23 mm

Stoe IPDSII diffractometer	2687 independent reflections
Monochromator: plane graphite	2076 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.117
T = 296 K	θmax = 26.0º
ω scan rotation method	θmin = 2.0º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −8→8
Tmin = 0.685, Tmax = 0.888	k = −12→10
6123 measured reflections	l = −23→25

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.1011P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.071	(Δ/σ)max = 0.001
wR(F2) = 0.169	Δρmax = 0.63 e Å−3
S = 1.01	Δρmin = −0.57 e Å−3
2687 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
192 parameters	Extinction coefficient: 0.054 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1114 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.43 (13)
Hydrogen site location: inferred from neighbouring sites

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.2767 (6)	0.3976 (4)	0.4834 (2)	0.0408 (9)
C2	0.2607 (6)	0.5458 (4)	0.5011 (2)	0.0380 (8)
C3	0.2552 (7)	0.6055 (4)	0.5626 (2)	0.0474 (9)
H3	0.2551	0.5526	0.6005	0.057*
C4	0.2499 (6)	0.7459 (4)	0.5652 (2)	0.0458 (9)
C5	0.2520 (6)	0.8278 (4)	0.5080 (2)	0.0444 (9)
C6	0.2545 (7)	0.7642 (4)	0.4471 (2)	0.0463 (9)
H6	0.2538	0.8157	0.4088	0.056*
C7	0.2579 (6)	0.6225 (4)	0.44509 (19)	0.0395 (8)
C8	0.2677 (6)	0.5285 (4)	0.3883 (2)	0.0438 (9)
C9	0.3137 (6)	0.2765 (5)	0.3758 (2)	0.0436 (10)
C10	0.4978 (6)	0.2535 (6)	0.3505 (3)	0.0598 (13)
H10	0.5993	0.3135	0.3599	0.072*
C11	0.5282 (7)	0.1425 (6)	0.3118 (3)	0.0624 (14)
H11	0.6517	0.1277	0.2946	0.075*
C12	0.3806 (7)	0.0500 (5)	0.2972 (2)	0.0527 (12)
H12	0.4041	−0.0263	0.2710	0.063*
C13	0.1967 (7)	0.0752 (5)	0.3229 (2)	0.0477 (11)
C14	0.1630 (6)	0.1861 (4)	0.3621 (2)	0.0466 (10)
H14	0.0397	0.2011	0.3795	0.056*
C15	0.0552 (10)	−0.1131 (6)	0.2632 (3)	0.0743 (16)
H15A	−0.0652	−0.1629	0.2605	0.112*
H15B	0.1584	−0.1749	0.2749	0.112*
H15C	0.0834	−0.0720	0.2216	0.112*
N1	0.2788 (5)	0.3963 (4)	0.41436 (16)	0.0412 (8)
O1	0.2907 (5)	0.2994 (3)	0.51795 (15)	0.0550 (8)
O2	0.2669 (6)	0.5562 (3)	0.33082 (15)	0.0616 (9)
O3	0.0389 (5)	−0.0085 (4)	0.3116 (2)	0.0749 (11)
Cl1	0.2389 (2)	0.82582 (13)	0.64049 (6)	0.0730 (4)
Cl2	0.25735 (16)	1.00342 (11)	0.51245 (6)	0.0578 (4)

	U11	U22	U33	U12	U13	U23
C1	0.047 (2)	0.0320 (19)	0.044 (2)	−0.0019 (18)	0.0005 (19)	0.0014 (16)
C2	0.0407 (16)	0.0300 (17)	0.043 (2)	−0.0036 (16)	−0.0006 (19)	−0.0017 (14)
C3	0.058 (2)	0.041 (2)	0.043 (2)	0.004 (2)	−0.004 (2)	−0.0045 (17)
C4	0.0455 (19)	0.044 (2)	0.047 (2)	0.003 (2)	−0.006 (2)	−0.0117 (17)
C5	0.0383 (15)	0.0338 (19)	0.061 (2)	0.0010 (17)	−0.006 (2)	−0.0052 (18)
C6	0.0487 (19)	0.037 (2)	0.053 (2)	0.006 (2)	0.001 (2)	0.0073 (17)
C7	0.0399 (17)	0.0360 (19)	0.043 (2)	−0.0027 (18)	0.001 (2)	0.0000 (15)
C8	0.049 (2)	0.041 (2)	0.042 (2)	0.004 (2)	0.0003 (18)	0.0012 (16)
C9	0.054 (2)	0.043 (2)	0.034 (2)	0.0034 (19)	0.0016 (15)	0.0006 (18)
C10	0.050 (2)	0.072 (3)	0.058 (3)	−0.006 (2)	0.007 (2)	−0.016 (3)
C11	0.057 (3)	0.069 (4)	0.061 (3)	0.007 (3)	0.010 (2)	−0.010 (3)
C12	0.075 (3)	0.043 (3)	0.040 (3)	0.012 (2)	0.002 (2)	−0.011 (2)
C13	0.066 (3)	0.035 (2)	0.042 (2)	−0.0022 (19)	−0.0012 (18)	−0.0046 (18)
C14	0.054 (2)	0.040 (2)	0.046 (2)	0.0013 (19)	0.0058 (18)	−0.001 (2)
C15	0.108 (4)	0.059 (3)	0.055 (3)	−0.021 (3)	−0.001 (3)	−0.013 (3)
N1	0.0523 (19)	0.0362 (17)	0.0351 (18)	−0.0028 (15)	0.0025 (15)	−0.0036 (13)
O1	0.087 (2)	0.0336 (15)	0.0445 (17)	0.0030 (16)	−0.0010 (15)	0.0009 (12)
O2	0.090 (2)	0.0525 (18)	0.0425 (18)	0.004 (2)	0.0015 (18)	0.0047 (14)
O3	0.081 (2)	0.067 (2)	0.076 (3)	−0.026 (2)	0.0145 (19)	−0.027 (2)
Cl1	0.1007 (9)	0.0574 (7)	0.0609 (8)	0.0176 (8)	−0.0121 (8)	−0.0238 (6)
Cl2	0.0536 (5)	0.0314 (5)	0.0883 (8)	0.0032 (5)	−0.0054 (6)	−0.0070 (5)

C1—O1	1.192 (5)	C9—C10	1.384 (6)
C1—N1	1.410 (5)	C9—C14	1.387 (6)
C1—C2	1.491 (5)	C9—N1	1.428 (5)
C2—C7	1.367 (5)	C10—C11	1.355 (7)
C2—C3	1.384 (6)	C10—H10	0.9300
C3—C4	1.368 (6)	C11—C12	1.388 (7)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.415 (6)	C12—C13	1.390 (6)
C4—Cl1	1.725 (4)	C12—H12	0.9300
C5—C6	1.389 (6)	C13—C14	1.364 (6)
C5—Cl2	1.713 (4)	C13—O3	1.376 (5)
C6—C7	1.381 (6)	C14—H14	0.9300
C6—H6	0.9300	C15—O3	1.424 (6)
C7—C8	1.479 (6)	C15—H15A	0.9600
C8—O2	1.205 (5)	C15—H15B	0.9600
C8—N1	1.395 (5)	C15—H15C	0.9600
O1—C1—N1	125.7 (4)	C14—C9—N1	120.2 (3)
O1—C1—C2	129.6 (4)	C11—C10—C9	119.2 (4)
N1—C1—C2	104.6 (3)	C11—C10—H10	120.4
C7—C2—C3	122.0 (4)	C9—C10—H10	120.4
C7—C2—C1	109.0 (3)	C10—C11—C12	122.0 (4)
C3—C2—C1	129.0 (4)	C10—C11—H11	119.0
C4—C3—C2	117.1 (4)	C12—C11—H11	119.0
C4—C3—H3	121.5	C11—C12—C13	117.9 (4)
C2—C3—H3	121.5	C11—C12—H12	121.1
C3—C4—C5	122.0 (4)	C13—C12—H12	121.1
C3—C4—Cl1	119.1 (3)	C14—C13—O3	115.7 (4)
C5—C4—Cl1	118.9 (3)	C14—C13—C12	121.1 (4)
C6—C5—C4	119.2 (4)	O3—C13—C12	123.2 (4)
C6—C5—Cl2	119.5 (3)	C13—C14—C9	119.6 (4)
C4—C5—Cl2	121.2 (3)	C13—C14—H14	120.2
C7—C6—C5	118.2 (4)	C9—C14—H14	120.2
C7—C6—H6	120.9	O3—C15—H15A	109.5
C5—C6—H6	120.9	O3—C15—H15B	109.5
C2—C7—C6	121.4 (4)	H15A—C15—H15B	109.5
C2—C7—C8	108.6 (3)	O3—C15—H15C	109.5
C6—C7—C8	130.0 (4)	H15A—C15—H15C	109.5
O2—C8—N1	125.4 (4)	H15B—C15—H15C	109.5
O2—C8—C7	128.7 (4)	C8—N1—C1	111.9 (3)
N1—C8—C7	105.9 (3)	C8—N1—C9	123.5 (3)
C10—C9—C14	120.3 (4)	C1—N1—C9	124.1 (3)
C10—C9—N1	119.5 (4)	C13—O3—C15	118.6 (4)
O1—C1—C2—C7	176.9 (5)	C14—C9—C10—C11	0.5 (8)
N1—C1—C2—C7	−1.1 (5)	N1—C9—C10—C11	−177.4 (4)
O1—C1—C2—C3	−1.1 (8)	C9—C10—C11—C12	−0.6 (9)
N1—C1—C2—C3	−179.1 (4)	C10—C11—C12—C13	0.8 (8)
C7—C2—C3—C4	−1.0 (7)	C11—C12—C13—C14	−0.9 (7)
C1—C2—C3—C4	176.7 (4)	C11—C12—C13—O3	179.7 (5)
C2—C3—C4—C5	−0.6 (8)	O3—C13—C14—C9	−179.7 (4)
C2—C3—C4—Cl1	178.9 (3)	C12—C13—C14—C9	0.9 (7)
C3—C4—C5—C6	1.7 (7)	C10—C9—C14—C13	−0.7 (7)
Cl1—C4—C5—C6	−177.9 (4)	N1—C9—C14—C13	177.2 (4)
C3—C4—C5—Cl2	−176.8 (4)	O2—C8—N1—C1	180.0 (5)
Cl1—C4—C5—Cl2	3.6 (5)	C7—C8—N1—C1	0.1 (5)
C4—C5—C6—C7	−1.0 (7)	O2—C8—N1—C9	7.6 (7)
Cl2—C5—C6—C7	177.4 (3)	C7—C8—N1—C9	−172.3 (4)
C3—C2—C7—C6	1.7 (7)	O1—C1—N1—C8	−177.5 (4)
C1—C2—C7—C6	−176.5 (4)	C2—C1—N1—C8	0.6 (5)
C3—C2—C7—C8	179.3 (4)	O1—C1—N1—C9	−5.2 (7)
C1—C2—C7—C8	1.2 (5)	C2—C1—N1—C9	172.9 (3)
C5—C6—C7—C2	−0.6 (7)	C10—C9—N1—C8	72.8 (6)
C5—C6—C7—C8	−177.7 (4)	C14—C9—N1—C8	−105.2 (5)
C2—C7—C8—O2	179.3 (5)	C10—C9—N1—C1	−98.6 (5)
C6—C7—C8—O2	−3.3 (9)	C14—C9—N1—C1	83.4 (5)
C2—C7—C8—N1	−0.8 (5)	C14—C13—O3—C15	170.2 (5)
C6—C7—C8—N1	176.6 (5)	C12—C13—O3—C15	−10.5 (8)